Pioneer or idiot? I had no idea when I first arrived in Havana on what would ultimately be a fool’s errand to catch sportfish on the fly.

This quixotic story does not have a happy ending in the traditional fishing sense. It doesn’t end with a trophy tarpon nor even me getting laid. This is simply the story of an almost broke American searching for sportfish on Cuba’s southern coast.

After 2 days in Havana gathering intelligence, I arrived in Trinidad on the Southern Coast of Cuba. I chose Trinidad simply because it was close to the legendary flats of Jardines de la Reina on Google Earth.

Trinidad at Sunset

I thought being in this somewhat larger town would give me access to the flats in an hour or so after finding the right guide. So far, I hadn’t encountered any fly-fishermen in Cuba or anyone who even knew what fly-fishing was. This prospect was equally exciting and worrisome. After dropping my bag off at the casa particular (ubiquitous B&B type situations where most economical travelers end up), I took a cab for 8 CUC pesos (equivalent to 8$) down to the Marina Hemingway. It was just before sunset and most people had gone home. I spoke with a sailor from New Zealand who told me to come back early the next morning when there would be more people.

After a big night out at the Casa de Musica, I crawled into the marina at around 8:30 the following morning. Not knowing their names in Spanish, I carried around pictures of tarpon, bonefish, and permit in my pocket. My borrowed 7wt Helios 2 had become an almost permanent attachment to my left hand. Upon seeing my rod the harbormaster came up to me and spoke two words in English: “fly-fishing” and “tarpon”. This sent an extremely hopeful chill up my spine that maybe I would be a pioneer after all. Up until this point I hadn’t known what fish I would be going after, but it was the beginning of tarpon season and the mangroves around Trinidad seemed prime for large tarpon.

Cuba is one of the only places in the world where politics and fly-fishing are inextricably linked. An official licensed charter cost 300 pesos, a pretty standard rate for a guided day of fly-fishing. I had $1000 pesos in cash for my whole trip, a fixed amount that could not be added to because of the American embargo.

Roadside Cuban propaganda about the 1961 U.S. Embargo (bloqueo)

Spending 300 pesos would mean that I would have to sleep outside or skip meals, or worst of all not go to the casa de musica at night. I explained this to the harbormaster and he pointed me to a short young man named Luisito, the only man in the harbor with a small enough skiff to handle the mangroves.

Luisito wore a faded red polo shirt and bright reflective sunglasses. He began to shake his head before I even started talking, saying in the same breath that the wind was too strong and that “está prohibido” – it’s illegal – a phrase I would begin to hear in almost every attempt to charter an unlicensed guide. He was right about the wind, and came around that he would take me out for 2 hours at a rate of 25$ an hour, a price slightly over the average monthly salary in Cuba. We decided to wait for the wind to die down and meet back at the harbor at noon.

I was ecstatic. I walked towards the beach feeling very proud of myself for having beaten the system and getting a shot at some fresh tarpon without paying retail. I walked a mile or so up the beach and stopped at a fallen down palm umbrella to set up the rod and aimlessly cast into the surf until noon. On my way back to the marina at 11 or so, a Canadian hotel guest noticed my fly rod and invited me over for some of his all-inclusive beers.

Now completely over the moon with myself, I strode confidently into the marina. Luisito had left for the day. I immediately began rationalizing, convincing myself that he had thought we agreed on 2 o’clock (dos), instead of 12 noon (doce) because the words are so similar in Spanish. I unsuccessfully casted to some needlefish off the dock and read the story of Theodore Roosevelt’s exploration of the Amazon, River of Doubt, which would ultimately become an apt title for my escapade.

At 2:30 I asked the next man who passed if he knew Luisito, and he turned out to be his brother. He gave me Luisito’s number and I went over to the harbormaster, a weasely little man who was very much beginning to dislike me, so that I could borrow his phone. I called Luisito who said that it was too windy (he wasn’t wrong), and we made plans to meet the following morning.

I was faced with a difficult choice at this point. I had read that about 100 miles northwest of Trinidad was Las Salinas National Park, which was supposed to have miles of flats that you could easily walk out to. If I were to go there I would have had to leave almost immediately to make it there by nightfall. Determined in my goal to catch a tarpon at this point, I elected to stay in Trinidad for the night. I headed to the beach to drink mojitos and eat rock lobster for unimaginably low prices, all under the comfort of my perceived arrangement with Luisito. However, placing my faith in Luisito turned out to be a mistake.

After another long night out at the Casa de Musica, I made my way to the marina at 9 o’clock the next morning. Luisito’s forest green skiff was tied to the dock, but there was no Luisito to be found. I received various reports that he had already left or not come in at all. I had now wasted 2 days of potential fishing time waiting for the flakiest captain since Captain Crunch. Completely outraged at this point and wishing that I had gone to Las Salinas, I left a particularly rude note in English under a rock on the front of Luisito’s skiff, much to the delight of some undoubtedly confused German tourists. It still makes me laugh to think of Luisito and his colleagues trying to decipher that note.

Hungover and incensed, I went to the beach where there was a young boy laying out deck chairs for the day. I asked him if there were any fishing villages around and he told me of El Puerto Pesquero Casilda, only 5 miles down the road. I ran to a taxi and he took me there immediately on a winding road through the mangroves. I was excited again, knowing this would probably be my last chance to take a shot at some virgin rolling tarpon.

Jumping Tarpon via @flywater_expeditions Instagram

In Puerto Casilda I made my way over to the docks. I stepped over a seemingly unimportant rope and two guards came running out. Both had hands on their revolvers. I put my hands somewhere between up and down and ask in hurried Spanish why I could not go onto the docks. I was met with hurried “está prohibido está prohibido” and cautiously retreated to the other side of the rope.

It might be worth noting at this point that I was probably the least likely person to ever walk into Puerto Casilda. I was wearing red board shorts, flip-flops, a Hatch trucker hat, and a bright yellow tank top that said Nantucket on it. I had a backpack on with what must have been a strange looking rod tube sticking out of it.

Laughing a little to myself and wondering what the hell just happened, I walked back into town I passed a schoolyard where some kids were playing. They laughed and waved to me. I waved back and approached a group of men to ask if they knew anyone who had a boat and would take me out. They looked shiftily at one another and one man ran off to ask another man something. He came back shaking his head and I was met with a chorus of “está prohibido”. Maybe if I had approached them individually, the answer might have been different.

Fuck it, I thought, and decided to walk into the mangroves myself to see if I could catch a tarpon unaided by boat. At 300 or 400 yards away from the road, the mud was up to the middle of my calves and after an especially deep step I panicked and plogged my way back to the road. I put my headphones in, put on “I Got a Name” by Jim Croce and began to walk back to the marina. My plan now was to attack the mangroves from the beach side, where I thought the ground might be a little firmer. I had my thumb out and a white pick-up truck picked me up and took me back to the Marina Hemingway without a word exchanged.

I was about to start walking up the beach when I ran into the Canadian guy who had given me beer the day before. I informed him of my predicament and he brought me some more beers and told me of another, closer fishing village called La Boca (the Mouth), so named because it was at the mouth of a river. He took me there immediately, even buying the necessary bus ticket for 2 pesos.

Upon arrival in La Boca, I was elated again at the sight of boats without armed guards. I spoke briefly with the harbormaster, a much nicer and unmistakably Cuban old man who brought over my new captain. Due to the illegality of what happened next, I will call him Anton. Anton, a squat and shrewd-looking young man, initially refused and then looked up hopefully and said “20 pesos”, a month’s salary in Cuba. I immediately agreed and myself, the Canadian, and Anton boarded his boat and headed up the river.

Fishing village of La Boca

Anton told me not to put the rod together until we were out of sight, so I stood victoriously at the bow of the boat like George Washington crossing the Delaware. For 280 pesos less than a licensed guide I was about to fly-fish in Cuba. I was more than confident I would succeed as I scanned the mangroves for the gigantic rolling tarpon that would be just around the next bend.

I put the rod together and tied on my most ambitious tarpon streamer. The Canadian had dropped the reel of a collapsible button rod he had brought in the river, so he sat contentedly back to watch me fish from the bow. The concept of fly-fishing bewildered Anton, but he said that he had seen it before in a cell phone game, which bewildered me. We weren’t seeing any tarpon so I just double-hauled and stripped from the middle of the river. I had Bluetooth speakers with me and put on the Allman Brothers Eat a Peach album, just happy to be fly-fishing on a boat. Anton was dumbfounded by the Bluetooth speakers and demanded an explanation. Laughing, I tried to explain that it was a radio of sorts, except I was the DJ, not really knowing how to explain the concept of Bluetooth in Spanish.

It worried me slightly that Anton did not know the word “tarpon”, nor did he recognize the picture. After about an hour of fishing to no avail, he informed me that there were only little fish in the river. The big fish, he said, were out to sea. He recognized the picture of the permit (which he probably thought was some type of jack or pompano), and said he would take me out to them at dawn the next morning. I settled for this and we all jumped in for a swim. Back at the boat, Anton shucked some oysters he had pulled up from the bottom and we ate them on the half-shell on the way back to the docks.

That night was my last in Trinidad. I was going to Havana the next afternoon to catch my flight back to Cancun. I slept about 45 minutes and took a cab down to La Boca to meet Anton. He was not waiting for me, which concerned me. Another fisherman took me to his house and he was not there either. Nobody knew where Anton was. I worried that the previous day’s expedition had gotten him in trouble, the fine for which was the loss of his boat and some jail time. I like to think that he took that 20 pesos and went on an absolute bender from which he was struggling to recover. Exhausted and defeated, I sat down on the beach in La Boca under the shade of a palm umbrella. A merciful young boy sold me a coconut for 1 peso that may have saved my life.

Fishless, I went back to Trinidad and took a shared taxi the 300 miles back to Havana.